5 Brutal Lessons About Entrepreneurship I Learned in My First Year as a Startup Founder

Lesson 1: you don't know everything.

Almost a year ago, I convinced one of my closest friends, Drew Reggie, to quit his job and join me on my entrepreneurship crusade.

I had left my job in advertising just a few months prior and was making a comfortable living as a freelance writer. He was about to finish his MBA, and had clearly verbalized his lack of excitement for what the future held: a high-paying cubicle job at a major company.

"I want to build something," he said. "You know, with employees. And financials. I don't want to freelance -- I want to build a company."

"Why won't you take the leap with me, then?" I asked, dozens of times over. "With the money we've saved up, do you really think we won't figure something out in a year?"

Twelve months later we have a full-time team and a company successful beyond our wildest dreams. Digital Press, named during one of our many coffee-on-an-apartment-balcony conversations, has been our attempt to empower the world's smartest people to share what they know. We work with carefully selected CEOs, entrepreneurs, investors, and venture capitalists (primarily at businesses doing $10M to $300M in revenue) to share their hard-earned insight with the internet. None of the atrocious writing most PR firms peddle as acumen. None of the ad-speak or jargon nobody finds helpful. Just the hard lessons learned and the personal stories of how these successful people learned them.

So, as a founder, I'd like to share some of the hard lessons I've learned over the past year, building Digital Press from ground zero.

Lesson No. 1: You know nothing (and that's OK).

I was extremely fortunate to have had a mentor before taking the entrepreneurial leap. Friend and fellow Inc. columnist Ron Gibori taught me more about life and business than I could have ever asked to learn on my own. But even after four years of mentorship, what I "knew" was still just theory.

I hadn't felt it yet.

Before I took the leap, Ron told me, "When everything turns to chaos, as the founder, you have to bring the calm."

I didn't understand what that meant until I started to feel the realities of building a company with other people's livelihoods at stake.

Entrepreneurship has humbled me. And I find it humbles a lot of young founders, who often set off to change the world only to feel the weight of their aspirations when they realize it doesn't happen overnight.

Theory means nothing until you've been in the trenches. So, be passionate. Set out to do something big. But remember, you won't truly know until you can say, "I've been there."

Lesson No. 2: Entrepreneurship without personal development is a disaster.

A year into my entrepreneurship I am astounded at how little the business world talks about the value of personal development.

I've done a lot in my 27 young years on this earth. I was a professional gamer as a teenager. I was a bodybuilder in college. But nothing, and I mean nothing, has tested me like entrepreneurship.

Throughout this past year, I found myself in moments where I would hyper-focus on the business, lose sight of myself, and then things in my life would crumble. Personal relationships. Health. Emotional well-being. Everything suffered, all because I felt like my business was my child, and I would go whatever distance to see it succeed.

This is unhealthy. And the moments you push too hard, you end up causing more damage than good.

I know I will be an entrepreneur for the rest of my life. There's no going back now. I am forever changed. But if there's one thing I hope to do for the entrepreneurial community along my journey, it's start larger dialogues about the importance of personal development while building a business.

If you lose yourself in the process, your company will suffer.

Lesson No. 3: Cash is your gasoline.

I'm lucky to have other successful business leaders in my life that have passed along words of wisdom. But one of the most important (and you learn this real fast as a startup founder) is the value of cash.

I have always been frugal, but entrepreneurship made me see the money I had as so much more than just a "savings account." Money started to have dozens of meanings: the ability to survive, the ability to innovate, the future of the company itself.

Without cash, your company dies.

Before we came up with the idea for Digital Press, we ate into our savings accounts. We helped each other cover our expenses. And the moment things clicked and we began to build a profitable business, we both shared the exact same mindset: "Keep as much cash in the company as possible."

This is one of those lessons you hear about, and can even understand on a theoretical level, but it's not until you start adding employees, and see your monthly payroll go up and up, that you truly understand.

Cash is your gasoline. You don't want to find yourself on the open road with an empty tank.

Lesson No. 4: The burden of opportunity is real.

A good problem to have is a problem nonetheless.

As an entrepreneur, one of the worst things you can do is chase too many rabbits at once. I have struggled with this through every aspect of my life, because when you're curious about the world you want to explore it all.

Part of what allows a business to flourish is simplicity. As another mentor of mine, Aaron Webber, would tell me: "Simplicity is velocity."

The moments we tried to build in too many directions at once, we failed. We overworked ourselves. We got burned out, even discouraged.

But when we were able to focus on improving one or two things at a time, we flew.

This is a lesson that fundamentally changed how I think about not just business, but every pursuit in life.

One thing at a time.

Lesson No. 5: Entrepreneurship is lonely.

Since not many other people seem to want to admit this, I guess I will.

Entrepreneurship is lonely. Nobody will know how hard you work at what you do. Nobody will give you the acknowledgment or the "pat on the back" you feel you deserve. Nobody will sit there, cheering you on, day in and day out. Nobody will take the fall when you mess up. Nobody will be able to tell you which direction is right or wrong.

Entrepreneurship is lonely because, by definition, it means choosing to go your own way.

This took me a while to accept and emotionally address within myself. Not only will your efforts go unacknowledged by the majority of people in your life (at least to the degree you'd like them to be), but at every step you will feel like you're letting someone down.

If you aren't letting your significant other down because you've been working for 17 straight hours, then you're letting your friend down for not calling them back, or you're letting your co-founder down by not responding to an issue fast enough, or you're letting your employees down by not getting them what they need -- or you're letting yourself down for not being able to do it all.

This is one of the hardest, most brutal truths about entrepreneurship:

In the process of trying to be great, you will fail at almost everything.

And do you know what? That's OK too.

Because at the end of the day, all you can do is your best -- and then wake up the next day and try again, and again, and again.